Off Market Aug 2024 for $4.3M

$5,591,253

Est. refi paymentEst. refi $11,018/mo

•

9,033

sq ft

253 Middlesex Rd, Darien, CT 06820

About this home

Welcome to luxury living at its finest! This impressive stone and shingle home redefines sophistication with meticulous craftsmanship and attention to detail. Nestled in the most convenient location, close to Schools, Metro-North, Darien Commons & all town amenities, offering the ultimate in lifestyle & convenience. Step inside to discover a world of elegance, where natural light floods the interiors, creating a warm & inviting atmosphere featuring custom millwork, soaring ceilings and fine details throughout. Entertain with style in the gourmet eat-in kitchen with a large island and butler's pantry, perfect for hosting gatherings of all sizes. French doors lead from the kitchen and living areas to covered porches, inviting you to bask in the serene views of the sparkling pool and lush surroundings. The main house boasts impeccable formal rooms and 5 spacious bedrooms, each with en suite baths, offering comfort and privacy for the entire family. 3-finished floors of living space, plus the bonus of a stunning separate structure featuring a private studio/office space with a cozy fireplace & cathedral ceiling paired with an additional two-car garage making a total of 5 garage spaces with Tesla charging station. The separate studio offers endless possibilities, be it a home office, artist's sanctuary, or private retreat. Experience the pinnacle of stone & shingle style living, from cozy family nights to grand celebrations, every moment will be cherished in this stunning home.

Single-familyProperty Type

2007Year Built

1.05 acresLot Size

$619Est. Price/Sq.Ft.

5 car garageParking

Listed by Taylor Tait • Houlihan Lawrence

Bought with Stephanie Hanford • Compass Connecticut, LLC

Source:Smart MLS #24000108

Redfin Estimate

$5,591,253

$1.2M since sold in August 2024$228K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 37.4% higher than the average sale price ($4.07M) of 6 comparable homes.

SOLD JUN 17, 2026
$3,775,000
A
5 beds6.5 baths7,200 sq ft
43 Stony Brook Rd, Darien, CT 06820
SOLD AUG 7, 2026
$3,250,000
B
5 beds5.5 baths5,226 sq ft
14 Revere Rd, Darien, CT 06820
SOLD JUL 23, 2026
$5,000,000
C
5 beds7 baths8,035 sq ft
473 Hollow Tree Ridge Rd, Darien, CT 06820
SOLD APR 28, 2026
$4,400,000
D
5 beds5 baths6,052 sq ft
15 Waterbury Ln, Darien, CT 06820
SOLD AUG 7, 2026
$4,200,000
E
5 beds4.5 baths5,678 sq ft
2 Roland Dr, Darien, CT 06820
SOLD AUG 6, 2026
$3,795,000
F
5 beds6.5 baths6,424 sq ft
39 Leeuwarden Rd, Darien, CT 06820

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Earn from this home

Sell

$1,879,230

Est. take-home

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Refinance

Est. cash available

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Rent

$7,506/mo

Redfin rental estimate

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Market trends in 06820, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

112.0%

+1.8% MoM

Median sale price

$3.0M

$202K MoM

Avg. days on market

12d

1 days MoM

Recently sold homes

30 MoM

New listings for sale

COMING SOON
$1,050,000
4 beds1.5 baths1,883 sq ft
29 Lynn Ct, Darien, CT 06820
OPEN SAT, 1PM TO 2:30PM
$949,000
2 beds1 bath910 sq ft
64 Noroton Ave, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$2,250,000
4 beds3.5 baths3,511 sq ft
1644 Boston Post Rd, Darien, CT 06820
$1,999,000
4 beds2.5 baths3,065 sq ft
2 Stony Brook Rd S, Darien, CT 06820
OPEN SUN, 1PM TO 3PM
$1,495,000
4 beds2 baths3,182 sq ft
1646 Boston Post Rd, Darien, CT 06820
COMING SOON
$7,500,000
5 beds7 baths10,213 sq ft
460 Middlesex Rd, Darien, CT 06820
$1,299,000
3 beds2 baths3,094 sq ft
53 Maple St, Darien, CT 06820
$3,950,000
5 beds5.5 baths5,500 sq ft
700 Hollow Tree Ridge Rd, Darien, CT 06820
See all

Provided by Redfin

Sale history for 253 Middlesex Rd

Date

Event

Price

Smart MLS #24000108

Aug 12, 2024

Sold

$4,398,000

$487/sq ft

Apr 19, 2024

Pending

—

Apr 3, 2024

Listed

$4,475,000

$495/sq ft

Smart MLS #99066064

Aug 4, 2014

Sold

$3,700,000

$410/sq ft

May 20, 2014

Listed

$3,825,000

$423/sq ft

Built by master craftsman in 2007 by Doherty & Deleo this 5 bedroom stone and shingle style Colonial has it all. Some of the many amenities and features are numerous including seven and one half baths, six fireplaces, a grand two-story foyer, master suite, custom country kitchen, magnificent interior trim details, coffered ceiling, wainscot paneling, nine foot ceilings, formal living and dining rooms, family room, exercise and playroom, media room, pool and pool house, five car garages, generator, attached gazebo and expansive terrace areas. Room and space from fun to formal this home will amaze you.

Public Records

Mar 5, 2007

Sold

$1,200,000

$133/sq ft

Public Records

Jul 30, 1992

Sold

$305,000

$34/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$45,610 (+2.2%)

$515,130 + $2,074,870

$2,590,000

2022

$44,626 (+2.3%)

$515,130 + $2,074,870

$2,590,000

2021

$43,616 (+3.1%)

$515,130 + $2,074,870

$2,590,000

2020

$42,295 (−6.4%)

$515,130 + $2,074,870

$2,590,000

2019

$45,174 (+5.6%)

$515,130 + $2,227,680

$2,742,810

2018

$42,773 (−0.5%)

$568,400 + $2,091,600

$2,660,000

2017

$42,986 (+2.5%)

$568,400 + $2,091,600

$2,660,000

2016

$41,948 (−5.4%)

$568,400 + $2,091,600

$2,660,000

2014

$44,337

$568,400 + $2,385,460

$2,953,860

Tax history for 253 Middlesex Rd

Year

Property tax

Land + Additions

Assessment*

2023

$45,610 (+2.2%)

$515,130 + $2,074,870

$2,590,000

2022

$44,626 (+2.3%)

$515,130 + $2,074,870

$2,590,000

2021

$43,616 (+3.1%)

$515,130 + $2,074,870

$2,590,000

2020

$42,295 (−6.4%)

$515,130 + $2,074,870

$2,590,000

2019

$45,174 (+5.6%)

$515,130 + $2,227,680

$2,742,810

2018

$42,773 (−0.5%)

$568,400 + $2,091,600

$2,660,000

2017

$42,986 (+2.5%)

$568,400 + $2,091,600

$2,660,000

2016

$41,948 (−5.4%)

$568,400 + $2,091,600

$2,660,000

2014

$44,337

$568,400 + $2,385,460

$2,953,860

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

1.05 Acres

Year renovated

—

Sq. Ft.

8,537

Year built

2007

Style

Single Family Residential

County

Fairfield County

APN

103873

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 5

Interior

Interior Information
Total Rooms: 16
Laundry Room Location: 2nd floor in Main house & in Pool House
Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
Fireplaces Total: 5
Cooling System: Central Air
Appliances Included: Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Exercise Room, Foyer, Mud Room
Basement Description: Full, Heated, Storage, Cooled, Interior Access, Partially Finished
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shingle, Stone, Wood
Exterior Features: Balcony, Gutters, Guest House, Covered Deck, Stone Wall, French Doors, Underground Sprinkler, Patio

Lot Information
Lot Description: Fence - Partial, Corner Lot, Treed

Pool Information
Swimming Pool
Pool Description: Gunite, Heated, Pool House, Spa, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: Beige

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 7933

Financial

Assessments Information
Assessed Value: $3,017,560

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Domestic
Heat Type: Baseboard, Hot Air, Radiant, Zoned
Heat Fuel Type: Oil, Propane
Fuel Tank Location: In Basement
Energy Features: Generator, Thermopane Windows

Location

School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Ox Ridge

Location Information
State: Connecticut
Nearby Amenities: Library, Medical Facilities, Park, Playground/Tot Lot, Public Rec Facilities, Public Transportation, Shopping/Mall
Directions: Middlesex Road to Libby Lane. 253 Middlesex is first home on right on Libby Lane.
County: Fairfield

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 8,537
Stories: 2.0
Lot Size: 1.05 acres
Style: Single Family Residential
Year Built: 2007
Year Renovated: —
County: Fairfield County
APN: 103873

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

Ox Ridge Elementary School

Public PreK-5 • Assigned • 1.7mi

10/10

Middlesex Middle School

Public 6-8 • Assigned • 0.6mi

10/10

Darien High School

Public 9-12 • Assigned • 0.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 99° expected this year, 16 days in 30 years

6/10 Wind Factor

72% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Darien, CT • 06820

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$5.31M – $6.43M

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Home values near 253 Middlesex Rd

Data from public records.

Address	Redfin Estimate
265 Middlesex Rd, Darien, CT 3 Beds \| 2.5 Baths \| 2002 Sq. Ft.	$1,774,732
231 Middlesex Rd, Darien, CT 3 Beds \| 2 Baths \| 1548 Sq. Ft.	$1,720,872

Address	Redfin Estimate
237 Middlesex Rd, Darien, CT 5 Beds \| 5.5 Baths \| 5949 Sq. Ft.	—
227 Middlesex Rd, Darien, CT 3 Beds \| 2.5 Baths \| 1500 Sq. Ft.	$1,813,377

Address	Redfin Estimate
245 Middlesex Rd, Darien, CT 5 Beds \| 5 Baths \| 6647 Sq. Ft.	$4,764,677
259 Middlesex Rd, Darien, CT 6 Beds \| 8 Baths \| 8552 Sq. Ft.	$6,901,311

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

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